As we grow older, it’s easy to end up out of the loop on style choices. We see it first with our parents. Then, one day, it’s us too. It often means we dress in clothes that are completely inappropriate for our age.

Sometimes it happens completely by accident. Other times, it’s a result of trying to be funny. However, for most of the people on this list, they are simply oblivious. That is the only way we can explain the ridiculous clothing items that they were caught wearing.

From offensive t-shirts that are demeaning to whole populations of people to jokes that are downright raunchy, these 40 people run the gamut. It begs the question, who bought them these hilarious outfits and do they even understand what they mean? That’s what we’re trying to figure out.